Octavio is one of a kind! We all had the best time despite the rainy, gray weather. Octavio humored us and took us on a trip of the Bay instead of the Gulf due to storms. He has offered up another evening so that we can experience the Sunset on the Gulf that we missed out on. Truly a great evening- highlighted by double rainbows and dolphins! If you are looking for an uptight-sophisticated, peaceful -romantic evening- look somewhere else, please. We brought drinks and snacks and had a fabulous adventure. As Octavio puts it- you can bring anything on-board so long as it's legal....He is hilarious- rich with stories and looking to make sure you have a great time! read more

See all

We went out with Captain Octavio on this 34ft sailboat. We had a blast. He was very accomadating and his prices were amazing. Next time we are visiting this area we will go out on his Sunset Cruise. read more

See all

We had a lovely evening on the water with Captain Alex last night. My husband and I went on a sunset sail and it was everything we were looking for! Alex is very nice and fun, the boat is beautiful, and being on the water at the end of the day was gorgeous! We will be back next year for sure. Highly recommend!! read more

Anna Maria Sailing adventures - Boating Near Me - Bradenton Beach, Florida

See all

Captain Alex was so nice and funny! we had an awesome and relaxing time, 10/10 recommended!!!

Alex was awesome. He's laid back and is fun to sail with. We were invited to help as much, or as little, as we were comfortable with. We'll definitely be back. read more

Anna Maria Sailing adventures - Me hoisting the sail - Boating Near Me - Bradenton Beach, Florida

Don't do it!!! Con artist. If THEY cancel you trip due to weather, you will not be refunded. Look at all the 1-star reviews on google, yelp, Facebook and travelocity. Currently filing with BBB and then taking civil action. They have stolen so much money over the years. Disgraceful. Even worse, they will repeatedly tell you that they're looking into the refund and tell you that they will get back to you. But they never get back to you. Which shows how fraudulent they truly are. read more

Great guide, wonderful person to spend the afternoon with! Captain Octavio is fun, personable, and laid back! Loved the afternoon would highly recommend to anyone! read more

See all

Loved loved loved this!! We did the deckhand sailing for 3 hours for four of us. First it was a rainy day and we were running late so Octovio accomodated us and the weather by starting about an hour and a half late when the rain stopped. There were free rum and cokes on the boat and we brought on sandwiches we made. He discussed with us our options and where we wanted to go and ended up doing both options he suggested!! One of our group was an amataur sailor and Octavio let him take the helm the whole trip so he basically got a three hour sailing lesson for free. Then Octavio cancelled the sunset tour because it was so foggy out anyway and gave us almost a full additional hour! We spent that hour going along the coast because another in our group was a bird watcher so we sought out all the birds. This was a great trip!! read more

Captain Alex stole from me! We scheduled a sailing trip after thanksgiving with our family. He texted us 30 minutes before we were to embark the day of the trip and said he was having engine issues. It ruined our trip! He said he should have it repaired and we could go out the next day. He didn't even reach out to us until late in the morning the next day to let us know it wasn't going to work out. As of today we still haven't been reimbursed for the $600. I filed a grievance with our credit card company, but who knows when we will be reimbursed. DO NOT USE THIS COMPANY. You can find a more professional group I'm certain! read more

This was my first time sailing, what fun! Octavio did an excellent job and was super awesome to hang out with . I can not wait to entertain future company by bringing them for a sail with Anna Maria Sailing. Very accommodating with drinks too! read more

Anna Maria Sailing adventures - Boating Near Me - Bradenton Beach, Florida

See all

Captain Octavio is a real character. His boat is small but he keeps the bar well stocked! $50 a person for a full 3+ hours is well worth it! The night we went out we saw dolphins and a beautiful sunset but it was windy and raining so we didn't get to do the sail. He let us take the wheel also which was cool. read more

Ships Ahoy Octavio! Last time was a hoot and we're looking forward to it again next time we're in town. This was a time to remember for the whole family!! read more

Captain Octavio and his boat ride were both amazing. He was so personable, and really was concerned with us having the best time. He provided all the drinks, which included endless bud light for me and my husband. We saw Dolphins, listened to great stories, and he even took us to where we got married so we could have a picture from the ocean. If you are looking for a laid back, great time then this is for you. We will be definitely coming back the next time we are here. read more

Captain Octavio was a gracious host and knowledgeable guide. Love supporting a local business. I come back often to visit friends and family and cannot wait to do this again. read more

Octavio is an amazing captain and host. He had us laughing all the way out to sea and back. Totally knows his stuff and is very comfortable on the water - coming from a somewhat experienced sailor! Can't wait to go back. read more

If there was an option to give 0 stars, I would have picked it!! The sunset cruise was a nightmare that required assistance from the Coast Guard. Why? Because Octavio was DRUNK and got us lost in the fog!! We didn't get off the boat until 9:30 and spent two hours terrified not knowing where we were and how we were going to get back!! On top of that there were not enough life jackets. read more

We had some friends visiting from up north so we thought we'd do something special with them. We went on the sunset cruise. There were 5 of us including my 8 year old son. My son had the chance to steer the boat. We had such a fun & relaxing time. Captain Octavio knew the waters well, the beer, rum & sodas were flowing, along with some very interesting stories. We all had a great time & saw a beautiful sunset. If you're looking for an uptight, fancy cruise then this is NOT for you but if you're looking for a laid back & fun time, then this IS for you. read more

Octavio was a NO SHOW for the sunset tour and texted us the boat wasn't working. We then called him from a different phone and said we wanted to book a tour. He butt dialed us on that line and was out partying with some people. He's a liar and cheat. Don't book him. read more

Octavia is a very fun and generous skipper that accommodated our wishes ~ we'll definitely make this one of "always do" adventures when we visit Anna Maria Island! A very good deal! read more

A friend and I booked a day cruise with Octavio. Showed up to the dock thirty minutes early, 1:30 hit (time we were supposed to depart) and he was no where in sight. We waited and waited and still nothing. Originally when I researched sailing charters I read nothing but good reviews about him, but as we waited that day I decided to check more reviews, come to find out he has no showed quite a few people. I called and called and no one answered. We wasted hours of our vacation and this company didn't have the decency to tell us they weren't coming. I finally received a called back later that day from the girlfriend of Octavio who seemed to be full of excuses, "I accidently took his phone, his boat broke down yesterday, we didn't see the booking." How unprofessional can you get!!! We stated we would like a refund, yet going on three weeks and still no refund!!! Every time my friends calls he says he'll call back. Its absolutely ridiculous. We did however find a great charter while we were there, BIMINI BAY SAILING. Nice and reliable, not as expensive and longer sailing charter. GO THERE!!!!!! read more